THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS

1962 ◽  
Vol 40 (7) ◽  
pp. 1326-1338 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer ◽  
P. A. J. Gorin
Keyword(s):  
Fatty Acids ◽  
Carbon Atom ◽  
Chain Length ◽  
Hydroxy Fatty Acid ◽  
Hydroxyl Group ◽  
Fatty Esters ◽  
Degree Of Unsaturation ◽  
Chain Compounds ◽  
Chain Lengths ◽  
Long Chain

The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C16 to C22, including several unsaturated esters, and even-numbered hydrocarbons from C16 to C24 are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C17 or C18 acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

Fermentation of long-chain compounds by Torulopsis apicola. IV. Products from esters and hydrocarbons with 14 and 15 carbon atoms and from methyl palmitoleate

1968 ◽  
Vol 46 (9) ◽  
pp. 1523-1528 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Carbon Chain ◽  
Hydroxy Fatty Acids ◽  
Hexadecenoic Acid ◽  
Hydroxy Acids ◽  
Chain Compounds ◽  
Long Chain ◽  
Direct Hydroxylation

Esters and hydrocarbons, containing 14 and 15 carbon atoms, are converted to the hydroxy fatty acid portions of glycosides by Torulopsis apicola in yields of 10–20%. When C-15 compounds are fermented, almost half of the hydroxy acids which are produced are 16-hydroxy C-17 acids. The carbon chain of the substrate is first lengthened by two carbon atoms and then hydroxylated. Direct hydroxylation also occurs, to a lesser extent, giving both 14-hydroxy- and 15-hydroxypentadecanoic acids. Similar results are obtained when C-14 compounds are used. Lengthening of the chain followed by hydroxylation gives rise to hydroxy C-16 acids and direct hydroxylation produces 13-hydroxy- and 14-hydroxytetradecanoic acids. Primary and secondary C-14 and C-15 alcohols were also isolated from the products of hydrocarbon fermentation (2.5–5 % yield). Methyl palmitoleate is converted to hydroxy fatty acids in yields of 40–70%, the major component of which is 16-hydroxy-cis-9-hexadecenoic acid.

The Use of N-alkanes for Estimating Intake and Passage Rate in Horses

1996 ◽  
Vol 1996 ◽  
pp. 98-98
Author(s):  
B M L McLean ◽  
R W Mayes ◽  
F D DeB Hovell
Keyword(s):  
Recent Work ◽  
Chain Length ◽  
Carbon Chain ◽  
Carbon Chain Length ◽  
Passage Rate ◽  
Forage Crops ◽  
Carbon Chains ◽  
Naturally Occurring ◽  
Chain Lengths ◽  
Long Chain

Alkanes occur naturally in all plants, although forage crops tend to have higher alkane contents than cereals. N-alkanes have odd-numbered carbon chains. They are ideal for use as markers in feed trials, because, they are inert, indigestible and naturally occurring, and can be recovered in animal faeces. Synthetic alkanes (even-numbered carbon chains) are available commercially and can also used as external markers. Dove and Mayes (1991) cite evidence indicating that faecal recovery of alkanes in ruminants increases with increasing carbon-chain length. Thus the alkane “pairs” (e.g. C35 & C36, and C32 & C33) are used in calculating intake and digestibility because they are long chain and adjacent to each other. However, recent work by Cuddeford and Mayes (unpublished) has found that in horses the faecal recovery rates are similar regardless of chain lengths.

scholarly journals Effect of different long-chain fatty acids on cholecystokinin releasein vitroand energy intake in free-living healthy males

2012 ◽  
Vol 108 (4) ◽  
pp. 755-758 ◽  
Author(s):  
Charlotte J. Harden ◽  
Adam N. Jones ◽  
Tannia Maya-Jimenez ◽  
Margo E. Barker ◽  
Natalie J. Hepburn ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Chain Length ◽  
Energy Intake ◽  
Acyl Chain ◽  
Dependent Manner ◽  
Long Chain Fatty Acids ◽  
Long Chain ◽  
Healthy Males ◽  
Cck Release ◽  
Chain Fatty Acids

Long-chain fatty acids have been shown to suppress appetite and reduce energy intake (EI) by stimulating the release of gastrointestinal hormones such as cholecystokinin (CCK). The effect of NEFA acyl chain length on these parameters is not comprehensively understood. Anin vitroscreen tested the capacity of individual NEFA (C12 to C22) to trigger CCK release. There was a gradient in CCK release with increasing chain length. DHA (C22) stimulated significantly (P < 0·01) more CCK release than all other NEFA tested. Subsequently, we conducted a randomised, controlled, crossover intervention study using healthy males (n18). The effects of no treatment (NT) and oral doses of emulsified DHA-rich (DHA) and oleic acid (OA)-rich oils were compared using 24 h EI as the primary endpoint. Participants reported significantly (P = 0·039) lower total daily EI (29 % reduction) with DHA compared to NT. There were no differences between DHA compared to OA and OA compared to NT. There was no between-treatment difference in the time to, or EI of, the first post-intervention eating occasion. It is concluded that NEFA stimulate CCK release in a chain length-dependent manner up to C22. These effects may be extended to thein vivosetting, as a DHA-based emulsion significantly reduced short-term EI.

scholarly journals Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women

1999 ◽  
Vol 81 (1) ◽  
pp. 37-44 ◽  
Author(s):  
Amanda E. Jones ◽  
Michael Stolinski ◽  
Ruth D. Smith ◽  
Jane L. Murphy ◽  
Stephen A. Wootton
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Chain Length ◽  
Time Course ◽  
Absorbed Dose ◽  
Dietary Fatty Acids ◽  
Fatty Acid Chain ◽  
Degree Of Unsaturation

The gastrointestinal handling and metabolic disposal of [1-13C]palmitic acid, [1-13C]stearic acid and [1-13C]oleic acid administered within a lipid–casein–glucose–sucrose emulsion were examined in normal healthy women by determining both the amount and nature of the13C label in stool and label excreted on breath as13CO2. The greatest excretion of13C label in stool was in the stearic acid trial (9.2 % of administered dose) whilst comparatively little label was observed in stool in either the palmitic acid (1.2 % of administered dose) or oleic acid (1.9 % of administered dose) trials. In both the palmitic acid and oleic acid trials, all of the label in stool was identified as being present in the form in which it was administered (i.e. [13C]palmitic acid in the palmitic acid trial and [13C]oleic acid in the oleic acid trial). In contrast, only 87 % of the label in the stool in the stearic acid trial was identified as [13C]stearic acid, the remainder was identified as [13C]palmitic acid which may reflect chain shortening of [1-13C]stearic acid within the gastrointestinal tract. Small, but statistically significant, differences were observed in the time course of recovery of13C label on breath over the initial 9 h of the study period (oleic acid = palmitic acid > stearic acid). However, when calculated over the 24 h study period, the recovery of the label as13CO2was similar in all three trials (approximately 25 % of absorbed dose). These results support the view that chain length and degree of unsaturation may influence the gastrointestinal handling and immediate metabolic disposal of these fatty acids even when presented within an emulsion.

The Leaf

2018 ◽  
Author(s):  
David R. Dalton
Keyword(s):  
Fatty Acids ◽  
Hydroxyl Group ◽  
Cross Linking ◽  
Hydroxyl Groups ◽  
Electromagnetic Spectrum ◽  
Hydroxystearic Acid ◽  
Reflection And Transmission ◽  
Visible Part ◽  
Leaf P ◽  
Long Chain

Grape leaves are thin and flat. As is common among leaves in general, they are composed of different sets of specialized cells. Today, on average, sunlight reaching their surface is about 4% ultraviolet (UV) (<400 nm), 52% infrared (IR) (>750 nm) and 44% visible (VIS) radiation. Little of the UV and IR are used by plants. As with other leaves that are green, only the red and blue ends of the visible part of the electromagnetic spectrum are absorbed, thus leaving green available by reflection and transmission. On the surface of the leaf (Figure 8.1), the cells of the outermost layer (the epidermis) are designed to protect the inner cells where the workings needed for gathering the sunlight used for photosynthesis and other chemistry necessary to the life of the plant are found. That is, the more delicate cells, beneath the epidermis, are involved in production of carbohydrates as well as the movement of nutrients in and products out of the leaf. The epidermis, exposed to the atmosphere, has cells that are usually thicker and are covered by a waxy layer made up of long- chain carboxylic acids that have hydroxyl groups (–OH) at or near their termini. These so-called omega hydroxy acids can then form esters using the hydroxyl group of one and the carboxylic acid of the next. This yields long-chain polyester polymers called “cutin.” As indicated in the earlier discussion of cells and, in particular, regarding the fatty acids of cell walls, the fatty acids found in the epidermis generally consist of an even number of carbon atoms, and for cutin, the sixteen carbon (palmitic acid) family (Figure 8.2) and the eighteen carbon family (oleic acid bearing a double bond or the saturated analogue stearic acid) are common. While one terminal hydroxyl group is usual (e.g., 16-hydroxypalmitic acid, 18-hydroxyoleic acid, or its saturated analogue 18-hydroxystearic acid) more than one (allowing for cross-linking) is not uncommon (e.g., 10,16-dihydroxypalmitic and 9,10,18-trihydroxystearic acid).

scholarly journals SELECTIVITY OF CANDIDA RUGOSA LIPASE IMMOBILIZED ONTO LAYERED DOUBLE HYDROXIDES AS CATALYST IN SYNTHESIS OF FATTY ACID ESTERS

2016 ◽  
Vol 78 (5-6) ◽  
Author(s):  
Mohd Basyaruddin Abdul Rahman ◽  
Siti Salhah Othman ◽  
Noor Mona Md Yunus
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Chain Length ◽  
Candida Rugosa ◽  
Candida Rugosa Lipase ◽  
Carbon Chain ◽  
Fatty Acid Esters ◽  
Carbon Chain Length ◽  
Chain Lengths ◽  
Acid Esters

The enzymatic selectivity of Lipase from Candida rugosa immobilized onto a calcined layered double hydroxide (CLDHs-CRL) towards the chain-length of fatty acids and alcohols in the synthesis of fatty acid esters was investigated.  The results showed that CMAN-CRL catalyzed the esterification process with fatty acids of medium chain lengths (C10-C14) effectively while, CNAN-CRL and CZAN-CRL exhibited high percentage conversion in fatty acids with carbon chain lengths of C8-C12 and C10-C18, respectively. In the alcohol selectivity study, CMAN-CRL showed high selectivity toward alcohols with carbon chain lengths of C4, C6 and C10.  On the other hand, both CNAN-CRL and CZAN-CRL exhibited rather low selectivity towards longer carbon chain length of alcohols. 

scholarly journals Fatty Acyl Esters of Hydroxy Fatty Acid (FAHFA) Lipid Families

Metabolites ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 512
Author(s):  
Paul L. Wood
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Fatty Acyl ◽  
Hydroxy Fatty Acids ◽  
Wax Esters ◽  
Hydroxyl Group ◽  
Cellular Functions ◽  
Health And Disease ◽  
Branched Chain

Fatty Acyl esters of Hydroxy Fatty Acids (FAHFA) encompass three different lipid families which have incorrectly been classified as wax esters. These families include (i) Branched-chain FAHFAs, involved in the regulation of glucose metabolism and inflammation, with acylation of an internal branched-chain hydroxy-palmitic or -stearic acid; (ii) ω-FAHFAs, which function as biosurfactants in a number of biofluids, are formed via acylation of the ω-hydroxyl group of very-long-chain fatty acids (these lipids have also been designated as o-acyl hydroxy fatty acids; OAHFA); and (iii) Ornithine-FAHFAs are bacterial lipids formed by the acylation of short-chain 3-hydroxy fatty acids and the addition of ornithine to the free carboxy group of the hydroxy fatty acid. The differences in biosynthetic pathways and cellular functions of these lipid families will be reviewed and compared to wax esters, which are formed by the acylation of a fatty alcohol, not a hydroxy fatty acid. In summary, FAHFA lipid families are both unique and complex in their biosynthesis and their biological actions. We have only evaluated the tip of the iceberg and much more exciting research is required to understand these lipids in health and disease.

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